Pyridine → Benzoic acid, 5-ethyl-2-[(phenylsulfonyl)amino]-

HRID 1725865노트

반응식

HRID 1725865 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[Si](C)(C)C.N1C=CC=CC=1.[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl>[CH2:11]([C:8]1[CH:9]=[CH:10][C:2]([NH:1][S:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:32])=[O:31])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])[CH3:12]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 7369Benzenesulfonyl chlorideHCID 77444862-Amino-5-ethylbenzoic acid

생성물 1

HCID 10402833Benzoic acid, 5-ethyl-2-[(phenylsulfonyl)amino]-

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

A solution of Example 1C (0.033 g, 0.200 mmol) in dichloromethane (1 mL) was treated with 1M chlorotrimethylsilane in dichloromethane (440 μL, 0.044 mmol) and pyridine (56.6 μL, 0.70 mmol), shaken for 4 hours at ambient temperature, treated with a solution of benzenesulfonyl chloride (0.042 g, 0.24 mmol) in dichloromethane (1 mL), and shaken for 16 hours at ambient temperature. The mixture was concentrated, the residue was acidified to pH 1.0 with 5% aqueous HCl, and the solution was extracted with dichloromethane. The extracts were washed sequentially with water and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by C18 reverse-phase HPLC with acetonitrile/water/0.5 mM ammonium acetate to provide the desired product. MS (ESI(+)) m/e 306 (M+H)+, 323 (M+NH4)+, 328 (M+Na)+; (ESI(−)) m/e 304 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.96 (br s, 1H), 7.78 (d, 2H), 7.73 (d, 1H), 7.64 (m, 1H), 7.55 (m, 2H), 7.42 (m, 2H), 2.54 (q, 2H), 1.10 (t, 3H).

후처리

  1. stirringshaken for 16 hours at ambient temperature
  2. concentrationThe mixture was concentrated
  3. extractionthe solution was extracted with dichloromethane
  4. washThe extracts were washed sequentially with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was purified by C18 reverse-phase HPLC with acetonitrile/water/0.5 mM ammonium acetate

출처 및 근거

ORD 기록
ord-6e78777a1b3c4b6199705a6af22e4115
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07491718B2

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